#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:37:51 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178574 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/84/4068412.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4068412
loop_
_publ_author_name
'Camadanli, Sebnem'
'Beck, Robert'
'Flörke, Ulrich'
'Klein, Hans-Friedrich'
_publ_section_title
;
 C−H Activation of Imines by Trimethylphosphine-Supported Iron
 Complexes and Their Reactivities
;
_journal_issue                   7
_journal_name_full               Organometallics
_journal_page_first              2300
_journal_paper_doi               10.1021/om800828j
_journal_volume                  28
_journal_year                    2009
_chemical_formula_sum            'C20 H42 Fe N P3'
_chemical_formula_weight         445.31
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6581(7)
_cell_length_b                   13.5905(10)
_cell_length_c                   18.7569(14)
_cell_measurement_reflns_used    6195
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.23
_cell_measurement_theta_min      2.16
_cell_volume                     2462.0(3)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2002)'
_computing_publication_material  'SHELXTL (Bruker, 2002)'
_computing_structure_refinement  'SHELXTL (Bruker, 2002)'
_computing_structure_solution    'SHELXTL (Bruker, 2002)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            29358
_diffrn_reflns_theta_full        28.20
_diffrn_reflns_theta_max         28.20
_diffrn_reflns_theta_min         1.85
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  430
_diffrn_standards_number         6216
_exptl_absorpt_coefficient_mu    0.812
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_correction_T_min  0.744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         3145
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0842P)²+0.3787P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1098
_reflns_number_gt                2570
_reflns_number_total             3145
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om800828j_si_001.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      Pnma
_cod_database_code               4068412
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Fe1 Fe 0.75693(3) 0.2500 0.419712(17) 0.02927(12) Uani 1 2 d S
P1 P 0.71404(6) 0.09441(3) 0.40436(3) 0.03979(15) Uani 1 1 d .
P2 P 0.95510(8) 0.2500 0.36118(4) 0.04116(18) Uani 1 2 d S
N1 N 0.8563(2) 0.2500 0.50907(10) 0.0313(4) Uani 1 2 d S
H1A H 0.9454 0.2500 0.5083 0.038 Uiso 1 2 calc SR
C1 C 0.6030(2) 0.2500 0.48831(13) 0.0323(5) Uani 1 2 d S
C2 C 0.4589(3) 0.2500 0.47675(15) 0.0418(6) Uani 1 2 d S
H2A H 0.4268 0.2500 0.4300 0.050 Uiso 1 2 calc SR
C3 C 0.3638(3) 0.2500 0.53076(17) 0.0455(6) Uani 1 2 d S
H3A H 0.2698 0.2500 0.5200 0.055 Uiso 1 2 calc SR
C4 C 0.4060(3) 0.2500 0.60139(17) 0.0481(7) Uani 1 2 d S
H4A H 0.3413 0.2500 0.6381 0.058 Uiso 1 2 calc SR
C5 C 0.5451(3) 0.2500 0.61608(15) 0.0432(6) Uani 1 2 d S
H5A H 0.5744 0.2500 0.6633 0.052 Uiso 1 2 calc SR
C6 C 0.6433(3) 0.2500 0.56169(13) 0.0330(5) Uani 1 2 d S
C7 C 0.7937(3) 0.2500 0.57025(13) 0.0322(5) Uani 1 2 d S
C8 C 0.8699(3) 0.2500 0.64143(13) 0.0414(6) Uani 1 2 d S
C9 C 0.8343(3) 0.15691(19) 0.68418(12) 0.0620(6) Uani 1 1 d .
H9A H 0.7368 0.1558 0.6941 0.093 Uiso 1 1 calc R
H9B H 0.8849 0.1570 0.7282 0.093 Uiso 1 1 calc R
H9C H 0.8589 0.0997 0.6569 0.093 Uiso 1 1 calc R
C10 C 1.0273(3) 0.2500 0.63054(17) 0.0620(9) Uani 1 2 d S
H10A H 1.0539 0.1931 0.6047 0.093 Uiso 1 1 calc PR
H10B H 1.0724 0.2500 0.6753 0.093 Uiso 0.50 1 calc PR
C11 C 0.7674(3) 0.0311(2) 0.32223(15) 0.0740(8) Uani 1 1 d .
H11A H 0.8659 0.0365 0.3166 0.111 Uiso 1 1 calc R
H11B H 0.7221 0.0608 0.2821 0.111 Uiso 1 1 calc R
H11C H 0.7420 -0.0371 0.3251 0.111 Uiso 1 1 calc R
C12 C 0.7842(3) 0.01228(16) 0.47244(14) 0.0630(6) Uani 1 1 d .
H12A H 0.7542 0.0338 0.5187 0.094 Uiso 1 1 calc R
H12B H 0.8835 0.0133 0.4704 0.094 Uiso 1 1 calc R
H12C H 0.7517 -0.0535 0.4641 0.094 Uiso 1 1 calc R
C13 C 0.5348(2) 0.05132(17) 0.40324(15) 0.0632(6) Uani 1 1 d .
H13A H 0.5332 -0.0184 0.3951 0.095 Uiso 1 1 calc R
H13B H 0.4851 0.0840 0.3658 0.095 Uiso 1 1 calc R
H13C H 0.4919 0.0657 0.4482 0.095 Uiso 1 1 calc R
C21 C 0.9545(4) 0.2500 0.26403(17) 0.0759(11) Uani 1 2 d S
H21A H 0.9078 0.1927 0.2470 0.114 Uiso 0.50 1 calc PR
H21B H 1.0476 0.2500 0.2468 0.114 Uiso 0.50 1 calc PR
C22 C 1.0791(3) 0.15030(19) 0.37978(15) 0.0670(6) Uani 1 1 d .
H22A H 1.0393 0.0884 0.3660 0.101 Uiso 1 1 calc R
H22B H 1.1000 0.1492 0.4298 0.101 Uiso 1 1 calc R
H22C H 1.1626 0.1613 0.3532 0.101 Uiso 1 1 calc R
H1 H 0.670(4) 0.2500 0.3535(19) 0.070(10) Uiso 1 2 d S
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1 Fe1 C1 78.93(9) . .
N1 Fe1 P1 102.105(17) . .
C1 Fe1 P1 86.71(2) . .
N1 Fe1 P1 102.105(17) . 7_565
C1 Fe1 P1 86.71(2) . 7_565
P1 Fe1 P1 153.16(3) . 7_565
N1 Fe1 P2 90.03(6) . .
C1 Fe1 P2 168.96(7) . .
P1 Fe1 P2 95.705(18) . .
P1 Fe1 P2 95.703(18) 7_565 .
C12 P1 C13 99.42(12) . .
C12 P1 C11 101.30(14) . .
C13 P1 C11 96.08(13) . .
C12 P1 Fe1 115.54(8) . .
C13 P1 Fe1 119.58(8) . .
C11 P1 Fe1 120.85(10) . .
C21 P2 C22 101.03(13) . .
C21 P2 C22 101.03(13) . 7_565
C22 P2 C22 94.75(18) . 7_565
C21 P2 Fe1 119.67(14) . .
C22 P2 Fe1 118.02(9) . .
C22 P2 Fe1 118.02(9) 7_565 .
C7 N1 Fe1 122.39(17) . .
C2 C1 C6 114.6(2) . .
C2 C1 Fe1 130.26(19) . .
C6 C1 Fe1 115.09(17) . .
C3 C2 C1 123.3(3) . .
C2 C3 C4 120.7(3) . .
C5 C4 C3 118.7(3) . .
C4 C5 C6 121.3(3) . .
C5 C6 C1 121.3(2) . .
C5 C6 C7 126.6(2) . .
C1 C6 C7 112.1(2) . .
N1 C7 C6 111.5(2) . .
N1 C7 C8 123.3(2) . .
C6 C7 C8 125.2(2) . .
C7 C8 C9 110.40(16) . .
C7 C8 C9 110.41(15) . 7_565
C9 C8 C9 110.8(2) . 7_565
C7 C8 C10 111.2(2) . .
C9 C8 C10 106.95(16) . .
C9 C8 C10 106.95(16) 7_565 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Fe1 N1 1.9316(19) .
Fe1 C1 1.966(2) .
Fe1 P1 2.1739(5) .
Fe1 P1 2.1739(5) 7_565
Fe1 P2 2.2064(8) .
P1 C12 1.826(2) .
P1 C13 1.828(2) .
P1 C11 1.838(2) .
P2 C21 1.822(3) .
P2 C22 1.842(2) .
P2 C22 1.842(2) 7_565
N1 C7 1.297(3) .
C1 C2 1.409(4) .
C1 C6 1.430(3) .
C2 C3 1.368(4) .
C3 C4 1.386(4) .
C4 C5 1.371(4) .
C5 C6 1.393(3) .
C6 C7 1.461(3) .
C7 C8 1.525(3) .
C8 C9 1.537(3) .
C8 C9 1.537(3) 7_565
C8 C10 1.533(4) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
N1 Fe1 P1 C12 -2.33(12) . .
C1 Fe1 P1 C12 -80.26(12) . .
P1 Fe1 P1 C12 -156.32(11) 7_565 .
P2 Fe1 P1 C12 88.93(11) . .
N1 Fe1 P1 C13 116.34(12) . .
C1 Fe1 P1 C13 38.41(13) . .
P1 Fe1 P1 C13 -37.65(13) 7_565 .
P2 Fe1 P1 C13 -152.40(11) . .
N1 Fe1 P1 C11 -124.91(13) . .
C1 Fe1 P1 C11 157.16(13) . .
P1 Fe1 P1 C11 81.10(14) 7_565 .
P2 Fe1 P1 C11 -33.65(12) . .
N1 Fe1 P2 C21 180.0 . .
C1 Fe1 P2 C21 180.0 . .
P1 Fe1 P2 C21 77.831(17) . .
P1 Fe1 P2 C21 -77.830(17) 7_565 .
N1 Fe1 P2 C22 56.46(11) . .
C1 Fe1 P2 C22 56.46(11) . .
P1 Fe1 P2 C22 -45.71(11) . .
P1 Fe1 P2 C22 158.63(11) 7_565 .
N1 Fe1 P2 C22 -56.46(11) . 7_565
C1 Fe1 P2 C22 -56.46(11) . 7_565
P1 Fe1 P2 C22 -158.63(11) . 7_565
P1 Fe1 P2 C22 45.71(11) 7_565 7_565
C1 Fe1 N1 C7 0.0 . .
P1 Fe1 N1 C7 -84.16(2) . .
P1 Fe1 N1 C7 84.16(2) 7_565 .
P2 Fe1 N1 C7 180.0 . .
N1 Fe1 C1 C2 180.0 . .
P1 Fe1 C1 C2 -76.981(17) . .
P1 Fe1 C1 C2 76.980(17) 7_565 .
P2 Fe1 C1 C2 180.000(1) . .
N1 Fe1 C1 C6 0.0 . .
P1 Fe1 C1 C6 103.019(17) . .
P1 Fe1 C1 C6 -103.020(17) 7_565 .
P2 Fe1 C1 C6 0.000(1) . .
C6 C1 C2 C3 0.0 . .
Fe1 C1 C2 C3 180.0 . .
C1 C2 C3 C4 0.0 . .
C2 C3 C4 C5 0.000(1) . .
C3 C4 C5 C6 0.000(1) . .
C4 C5 C6 C1 0.000(1) . .
C4 C5 C6 C7 180.0 . .
C2 C1 C6 C5 0.0 . .
Fe1 C1 C6 C5 180.0 . .
C2 C1 C6 C7 180.0 . .
Fe1 C1 C6 C7 0.0 . .
Fe1 N1 C7 C6 0.0 . .
Fe1 N1 C7 C8 180.0 . .
C5 C6 C7 N1 180.0 . .
C1 C6 C7 N1 0.0 . .
C5 C6 C7 C8 0.0 . .
C1 C6 C7 C8 180.0 . .
N1 C7 C8 C9 -118.57(17) . .
C6 C7 C8 C9 61.43(17) . .
N1 C7 C8 C9 118.57(17) . 7_565
C6 C7 C8 C9 -61.43(17) . 7_565
N1 C7 C8 C10 0.0 . .
C6 C7 C8 C10 180.0 . .
